Rogue Negotiators, Gemini Pulled, Apple’s AI Shift, Disappearing CAPTCHAs, and More! - SWN #526

In the AI era, cybersecurity is undergoing a fundamental shift as AI agents transform both the speed and scale of attacks. In this interview, Gibb Witham, President and Chief Financial Officer of Hack The Box, explains why organizations must move beyond assumed AI capability toward measurable, validated cyber readiness for both humans and AI systems. Drawing on real-world benchmarks, agentic AI testing, and hands-on training, Witham outlines how security teams can safely adopt AI by proving performance under pressure. The discussion highlights why the future of cybersecurity depends on training, testing, and reinforcing human and AI operators together before they are trusted in critical environments. This segment is sponsored by Hack The Box. Visit https://securityweekly.com/hacktheboxrsac to learn more about them! As credential-based attacks continue to dominate headlines, many organizations are realizing that identity alone is no longer a sufficient control. This conversation explores the shift toward device-based access enforcement and why tying access to both user and device is becoming critical. We’ll discuss how this evolution is reshaping Zero Trust strategies across modern environments. This segment is sponsored by ThreatLocker. Visit https://securityweekly.com/threatlockerrsac to learn more about them! Visit https://www.securityweekly.com/swn for all the latest episodes! Show Notes: https://securityweekly.com/swn-568

The future of secure software is going through a mix of skills expected of humans and skills files created for LLMs. We might even posit that appsec as a discipline will fade (and that might not even be a bad thing!). Keith Hoodlet describes the skills he was looking for in building teams of security researchers and why there's still an emphasis on the ability to learn about and understand how software is built. But figuring out what skills will get you hired and what skills are valuable to invest in still feels daunting to new grads and others entering the security industry. We discuss where the role of appsec seems to be heading and a few of the security and software fundamentals that can help you follow that direction. Segment resources https://bsidessf2026.sched.com/event/2E1h4/we-pwn-the-night-growing-leading-an-31337-security-research-team?iframe=yes&w=100%&sidebar=yes&bg=no https://drive.google.com/file/d/1_zLH8vuHU1XOjEyk85WecQwSByDwxAmQ/view?pli=1 https://securing.dev/posts/if-i-were-eighteen-again/ https://research.nvidia.com/labs/lpr/slm-agents/ Then, we rebroadcast two interviews from RSAC 2026. The Identity Crisis of Agentic AI Identity security is being stretched between legacy infrastructure that was never built to be secure and rapidly emerging AI agents and non-human identities that organizations are quickly adopting. As AI accelerates, identity risk grows alongside it, making agentic security fundamentally an identity challenge—because the more access AI has, the greater both its power and potential risk. In this session, Ron Rasin explores how past gaps in areas like Active Directory and machine identities created today’s blind spots, and why identity must now act as the control plane for AI-driven enterprises, with real-time enforcement before access is granted. He also highlights new innovations and partnerships enabling embedded identity controls across human, non-human, and AI identities, emphasizing that at machine speed, reactive security is no longer enough. To learn more about Silverfort and their AI Agent product, visit https://securityweekly.com/silverfortrsac. Privileged by Design: AI Agents and the New Identity Risk to Production Systems At RSAC this year, the AI conversation is getting more practical. Less “look what agents can do” and more “who’s actually in control when an autonomous system can take real actions across business apps and infrastructure.” The Moltbook breach and the growing attention on OpenClaw-style agent vulnerabilities put real weight behind that question because they show how quickly agent ecosystems can scale past oversight. Today we’re talking with Shashwath, CEO of P0 Security, about why identity and authorization are the quiet enablers of modern AI, where teams are losing control as non-human identities explode and what security leaders can do to keep innovation moving without turning access sprawl into enterprise risk. To learn more about P0 Security, visit: https://securityweekly.com/p0rsac. Visit https://www.securityweekly.com/asw for all the latest episodes! Show Notes: https://securityweekly.com/asw-376

Interview with Helen Patton about her new book, Switching to Cyber Helen joins us to discuss her second book, "Switching to Cyber." Her first book discussed strategies for handling various stages of the cybersecurity career, while this one, co-written with Josiah Dykstra, provides a guide for switching to cyber mid-career. Check out her book, Switching to Cyber: The Mid-Career Guide to Launching a Cybersecurity Career: on Amazon on Barnes & Noble and on the publisher's website Interview with Lenny Zeltzer: Reflections on Being a CISO After a cybersecurity career in various roles, doing everything from product management to malware analysis training, Lenny spent 6 years in the CISO seat at Axonius, from near the inception of the company through its growth from its modest Series A stage in 2019 to the present, with nearly a billion in funding today. Lenny's CISO Essays: What Being a CISO Taught Me About Security Leadership As a CISO, Are You a Builder, Fixer, or Scale Operator? The Chief Insecurity Officer Interview with Alexandre Sieira: The state of TPCRM is shifting The gold standard for third party cyber risk management has long been the humble questionnaire. While we've seen security rating services companies generate scores by scanning a company's external resources. Both approaches are widely considered inaccurate for either creating trust relationships or determining the true risk of doing business with a third party. Every analysis of this problem comes to the same conclusion: without internal data about the state of systems and the security program, TPCRM can't improve substantially. Most this believe this to be an impossible problem: third parties would never share data this sensitive with a customer and first parties assume the same. What if they did? That's exactly the premise behind Tenchi Security, and Alexandre joins us to talk about how they've accomplished the 'impossible' in Brazil and aim to expand their success to the US. Resources: Thoughts from a panel discussion at a recent FS-ISAC event, shared on LinkedIn Predicts 2026: Third-Party Cybersecurity Risk Management Evolves for the AI Era (Gartner Subscribers only, sorry) Visit https://www.securityweekly.com/esw for all the latest episodes! Show Notes: https://securityweekly.com/esw-452

In this two-part interview, Rinoa Poison explores the mechanics of modern scams, the role of AI in making them more convincing, and the growing world of scam baiting. She also discusses the tactics, technical setups, and safety considerations behind wasting scammers’ time. Visit https://www.securityweekly.com/swn for all the latest episodes! Show Notes: https://securityweekly.com/swn-567

In this segment, we will explore some pretty awesome tools for scanning the Internet, with a focus on network edge devices. We'll bring it all together with Claude Code and look at some sample results. Tools include: Shodan | Passive recon — query existing scan data for exposed devices, services, and vulns | Passive (API) | Instant (no packets sent) ZMap | Host discovery — find live hosts with open ports | L4 (TCP SYN, UDP, ICMP) | Millions of packets/sec ZGrab2 | Application-layer handshakes — grab banners, certs, headers | L7 (30+ protocol modules) | Thousands of hosts/sec Nerva | Service fingerprinting — identify 140+ protocols with metadata, CPEs, technology stacks | L7 (TCP, UDP, SCTP) | Fast, concurrent Nuclei | Template-based vulnerability scanning — default creds, exposed panels, known CVEs | L7 (HTTP, network) | Hundreds of targets/min Shannon | Vulnerability exploitation — AI-powered whitebox pentesting of web apps | Application | ~1-1.5 hrs per target edgescan.py | Automated pipeline — orchestrates all tools above into a single command | Orchestration | End-to-end Visit https://www.securityweekly.com/psw for all the latest episodes! Show Notes: https://securityweekly.com/psw-919

With Q-day getting closer, regulatory guidance pushing firms to migrate to quantum security in the next five years, and an extensive remediation backlog waiting to be discovered, security leaders must start their quantum security migration today. Easier said than done. In this Say Easy, Do Hard segment, we discuss the quantum-safe journey using a framework for crypto-agility. In part 1, we define cryptographic agility, or crypto-agility for short, and why it's important. Crypto-agility is not just about transitioning to quantum-safe cryptography in the nimblest way possible, and it’s not something that can be achieved merely by updating encryption algorithms and protocols. Instead, you need to adapt your organization’s cryptographic architecture, automation, and governance to allow for greater control and flexibility. In part 2, we discuss a framework for discovery, prioritization, and remediation while keeping crypto-agility in mind. A quantum-safe journey requires: Inventory of Systems With Non-Quantum-Safe Algorithms And Protocols System Prioritization, Leading To A Migration Roadmap Remediation, Including Vendors And Partners Once a distant possibility, Q-Day is quickly approaching. Are you ready for 2030? Segment Resources: https://pqcc.org/wp-content/uploads/2025/05/PQC-Migration-Roadmap-PQCC-2.pdf https://pqcc.org/wp-content/uploads/2025/06/PQCC-Inventory-Workbook.xlsx https://qramm.org/learn/cryptoscan-guide.html https://research.ibm.com/blog/quantum-safe-cbomkit Visit https://www.securityweekly.com/bsw for all the latest episodes! Show Notes: https://securityweekly.com/bsw-440

Rinoa Poison joins Security Weekly News to break down the world of scam baiting, how modern scams are evolving, and why AI is making fraud harder to spot. In this two-part conversation, she shares how scam baiters operate, the risks involved, and what everyday people should know. Visit https://www.securityweekly.com/swn for all the latest episodes! Show Notes: https://securityweekly.com/swn-566

So much of appsec’s efforts can be consumed by vuln management and a race to patch security flaws. But that’s more a symptom of the ease of scanning and the volume of CVEs. Erik Nost walks through the principles behind proactive security, why the concept sounds familiar to secure by design, and why organizations still struggle with creating effective practices for visibility. Resources https://www.forrester.com/blogs/proactive-security-platforms-will-cumulate-visibility-prioritization-and-remediation/ Visit https://www.securityweekly.com/asw for all the latest episodes! Show Notes: https://securityweekly.com/asw-375

Interview with Kara Sprague - The AI Fix for Infrastructure’s Oldest Security Risks. Critical infrastructure, often built on decades-old systems and legacy code, remains vulnerable to cyberattacks. From pipelines and energy grids to transportation networks, we break down where critical infrastructure is vulnerable and how AI could potentially help strengthen defenses. Interview with Mike Privette - The State of the Cybersecurity Market Here at ESW, we use Mike Privette's Security, Funded newsletter to prepare for every news segment. His newsletter covers the latest fundings, acquisitions, public market performance, layoffs, and other pertinent market details every week. We particularly enjoy the weekly Vibe Check. In this interview, he joins us for the third year in a row, to discuss the most interesting insights from his annual State of Market Report. Post recording Adrian here: Whooooo, so this conversation was SO good, I decided to punt the news segment in favor of a part 2 with Mike, so enjoy! Also, though I punted the news segment, I did collect these stories and annotated them, so I think there's still some value in leaving them in the show notes. Scroll down for the links and my comments on each of these! Weekly Enterprise News Finally, in the enterprise security news, funding announcements seem to be ramping up before RSA Should security architects be shifting right? How McKinsley’s AI platform got hacked… by AI Amazon is having a bad time with AI lately Europe announces a Google Workspace/Microsoft 365 replacement Robot dogs are apparently guarding datacenters now Some much needed security humor in our squirrel stories before we all fly to San Francisco and lose our minds for a week All that and more, on this episode of Enterprise Security Weekly. Visit https://www.securityweekly.com/esw for all the latest episodes! Show Notes: https://securityweekly.com/esw-451

Macbeth, Ahab, Peewee Herman, Microsoft, Zoom, Vibe Hacking, SharePoint, Meta, AgeID, Josh Marpet, and More on this episode of the Security Weekly News. Visit https://www.securityweekly.com/swn for all the latest episodes! Show Notes: https://securityweekly.com/swn-565